data_wh415a # racemic _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H14 N2, H O3 P, 2.230(H2 O)' _chemical_formula_sum 'C5 H19.47 N2 O5.24 P' _chemical_formula_weight 222.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 31.075(2) _cell_length_b 31.075(2) _cell_length_c 6.1875(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5174.5(6) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2123 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 22.42 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2167 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11694 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2270 _reflns_number_gt 1419 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2270 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16424(10) 0.13329(10) 1.0671(4) 0.0488(7) Uani 1 1 d . . . H1A H 0.1521 0.1460 1.1806 0.059 Uiso 1 1 calc R . . H1B H 0.1426 0.0975 1.0599 0.059 Uiso 1 1 calc R . . C2 C 0.16336(10) 0.15629(10) 0.8542(4) 0.0472(7) Uani 1 1 d . . . H2A H 0.1732 0.1418 0.7393 0.057 Uiso 1 1 calc R . . H2B H 0.1299 0.1494 0.8241 0.057 Uiso 1 1 calc R . . C3 C 0.24875(9) 0.22250(10) 0.9113(4) 0.0430(7) Uani 1 1 d . . . H3A H 0.2700 0.2583 0.9195 0.052 Uiso 1 1 calc R . . H3B H 0.2611 0.2104 0.7958 0.052 Uiso 1 1 calc R . . C4 C 0.25143(9) 0.19952(9) 1.1228(4) 0.0388(6) Uani 1 1 d . . . H4 H 0.2419 0.2143 1.2400 0.047 Uiso 1 1 calc R . . C5 C 0.30388(11) 0.20969(12) 1.1653(5) 0.0648(9) Uani 1 1 d . . . H5A H 0.3047 0.1948 1.3000 0.097 Uiso 1 1 calc R . . H5B H 0.3262 0.2449 1.1722 0.097 Uiso 1 1 calc R . . H5C H 0.3139 0.1958 1.0505 0.097 Uiso 1 1 calc R . . N1 N 0.19754(7) 0.21057(8) 0.8604(3) 0.0394(5) Uani 1 1 d . . . H1C H 0.1972 0.2238 0.7314 0.047 Uiso 1 1 calc R . . H1D H 0.1871 0.2242 0.9609 0.047 Uiso 1 1 calc R . . N2 N 0.21563(8) 0.14508(7) 1.1178(3) 0.0404(5) Uani 1 1 d . . . H2C H 0.2256 0.1309 1.0179 0.048 Uiso 1 1 calc R . . H2D H 0.2158 0.1319 1.2472 0.048 Uiso 1 1 calc R . . P1 P 0.15266(2) 0.24525(3) 0.38144(10) 0.0360(2) Uani 1 1 d . . . H1 H 0.1582 0.2896 0.4167 0.043 Uiso 1 1 calc R . . O1 O 0.14844(6) 0.23776(7) 0.1386(2) 0.0463(5) Uani 1 1 d . . . O2 O 0.10577(6) 0.20855(7) 0.4993(3) 0.0542(5) Uani 1 1 d . . . O3 O 0.19835(6) 0.24666(7) 0.4717(3) 0.0503(5) Uani 1 1 d . . . O4 O 0.29532(8) 0.31123(7) 0.3594(3) 0.0701(6) Uani 1 1 d . . . H41 H 0.2634 0.2900 0.4100 0.084 Uiso 1 1 d R . . H42 H 0.3127 0.3114 0.4799 0.084 Uiso 1 1 d R . . O5 O 0.05851(10) 0.10381(10) 0.4680(6) 0.1335(13) Uani 1 1 d . . . H51 H 0.0813 0.1396 0.4829 0.160 Uiso 1 1 d R . . H52 H 0.0280 0.0981 0.4446 0.160 Uiso 1 1 d R . . O6 O 0.06189(10) 0.02022(10) -0.0346(6) 0.239(15) Uiso 0.230(11) 1 d PR . . H61 H 0.0748 0.0280 -0.1687 0.287 Uiso 0.230(11) 1 d PR . . H62 H 0.0368 0.0268 -0.0347 0.287 Uiso 0.230(11) 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0511(17) 0.0393(15) 0.0521(17) 0.0057(13) 0.0044(13) 0.0197(14) C2 0.0500(17) 0.0513(17) 0.0468(16) -0.0061(13) -0.0081(13) 0.0302(15) C3 0.0426(16) 0.0460(16) 0.0437(16) 0.0105(12) 0.0070(12) 0.0246(13) C4 0.0447(15) 0.0426(15) 0.0353(14) -0.0008(11) -0.0013(11) 0.0265(13) C5 0.057(2) 0.075(2) 0.069(2) 0.0084(17) -0.0036(16) 0.0375(18) N1 0.0518(14) 0.0491(13) 0.0281(11) 0.0067(9) 0.0036(9) 0.0333(12) N2 0.0603(15) 0.0439(13) 0.0296(11) 0.0063(9) 0.0063(10) 0.0354(12) P1 0.0401(4) 0.0459(4) 0.0270(3) -0.0027(3) -0.0019(3) 0.0253(3) O1 0.0478(11) 0.0748(13) 0.0271(9) -0.0018(9) -0.0016(8) 0.0387(10) O2 0.0418(11) 0.0716(13) 0.0395(11) -0.0077(9) 0.0066(8) 0.0210(10) O3 0.0445(11) 0.0735(13) 0.0342(10) 0.0096(9) -0.0029(8) 0.0305(10) O4 0.0603(14) 0.0619(14) 0.0661(15) 0.0080(11) 0.0009(10) 0.0140(11) O5 0.0748(18) 0.0726(19) 0.257(4) -0.006(2) -0.012(2) 0.0395(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.483(3) . ? C1 C2 1.506(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N1 1.478(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.476(3) . ? C3 C4 1.513(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.489(3) . ? C4 C5 1.520(4) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? N1 H1C 0.9000 . ? N1 H1D 0.9000 . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? P1 O3 1.5059(18) . y P1 O2 1.5144(18) . y P1 O1 1.5161(16) . y P1 H1 1.3200 . ? O4 H41 0.9283 . ? O4 H42 0.9188 . ? O5 H51 0.9781 . ? O5 H52 0.8854 . ? O6 O6 1.752(3) 11 ? O6 O6 1.752(3) 12 ? O6 H61 0.9006 . ? O6 H62 0.8993 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C2 109.9(2) . . ? N2 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N2 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? N1 C2 C1 110.2(2) . . ? N1 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N1 C3 C4 111.9(2) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C3 109.4(2) . . ? N2 C4 C5 110.7(2) . . ? C3 C4 C5 111.0(2) . . ? N2 C4 H4 108.6 . . ? C3 C4 H4 108.6 . . ? C5 C4 H4 108.6 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 N1 C2 111.20(19) . . ? C3 N1 H1C 109.4 . . ? C2 N1 H1C 109.4 . . ? C3 N1 H1D 109.4 . . ? C2 N1 H1D 109.4 . . ? H1C N1 H1D 108.0 . . ? C1 N2 C4 112.68(19) . . ? C1 N2 H2C 109.1 . . ? C4 N2 H2C 109.1 . . ? C1 N2 H2D 109.1 . . ? C4 N2 H2D 109.1 . . ? H2C N2 H2D 107.8 . . ? O3 P1 O2 112.43(10) . . y O3 P1 O1 112.34(10) . . y O2 P1 O1 112.62(10) . . y O3 P1 H1 106.3 . . ? O2 P1 H1 106.3 . . ? O1 P1 H1 106.3 . . ? H41 O4 H42 98.5 . . ? H51 O5 H52 109.8 . . ? O6 O6 O6 114.22(18) 11 12 ? O6 O6 H61 120.5 11 . ? O6 O6 H61 107.6 12 . ? O6 O6 H62 90.1 11 . ? O6 O6 H62 32.8 12 . ? H61 O6 H62 105.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C1 C2 N1 -57.3(3) . . . . ? N1 C3 C4 N2 54.1(3) . . . . ? N1 C3 C4 C5 176.6(2) . . . . ? C4 C3 N1 C2 -56.8(3) . . . . ? C1 C2 N1 C3 57.8(3) . . . . ? C2 C1 N2 C4 57.0(3) . . . . ? C3 C4 N2 C1 -54.8(3) . . . . ? C5 C4 N2 C1 -177.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1C O3 0.90 1.75 2.648(3) 176 . N1 H1D O1 0.90 1.83 2.701(3) 164 1_556 N2 H2C O1 0.90 1.80 2.680(3) 166 11_556 N2 H2D O2 0.90 1.77 2.665(3) 173 11_557 O4 H41 O3 0.93 1.82 2.746(3) 172 . O4 H42 O4 0.92 1.81 2.724(2) 171 5 O5 H51 O2 0.98 1.89 2.830(3) 161 . O5 H52 O5 0.89 2.05 2.829(3) 147 12_556 O6 H61 O5 0.90 2.01 2.912(7) 180 11 O6 H62 O6 0.90 2.04 2.942(5) 180 2 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.244 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.044